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US 6,313,349 B1Granted
Aminophenol compound, method for producing the same and intermediate in synthesizing the same
AssigneeFuji Photo Film Co., Ltd.
InventorTadahisa Sato
Life of this patent
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Abstract
Described are Aminophenol compounds having a nitrogen-linking substituent at the 5-position which are intermediates in synthesizing benzoazole compounds useful as organic luminescence device materials, and a method for producing the same.
Claims15
A method for producing an aminophenol compound represented by the following formula (I) via a compound represented by the following formula (II):
- wherein Y1, represents an N-alkyl-N-arylamino group, a diarylamino group, or a five-membered nitrogen-containing aromatic heterocyclic group having an endocyclic nitrogen atom bonded to the benzene ring, provided that when Y1 is a substituted diphenylamino group, it is a diphenylamino group having at least one substituent selected from a group consisting of alkyl, aryl, alkoxy, aryloxy, dialkylamino, N-alkyl-N-arylamino and diarylamino groups;
- R1, R2 and R3 each represents a hydrogen atom or a substituent;
- X1 represents an acid group of an inorganic or organic acid;
- and m is from 0 to 2;
- and
- wherein Y1, R1, R2, and R3 are each as defined above;
- and R4 represents an alkyl group, comprising one of the following methods (a) and (b):
- (a) converting the —OR4 group in formula (II) into an —OH group by using a dealkylation reaction or a nucleophilic substitution reaction into a benzene ring by hydroxyl ion,
- reducing the nitro group in formula (II) by using a metal reduction method or a catalytic hydrogen reduction method, and
- treating the product with HX1,
- when R4 in the formula (II) is an unsubstituted alkyl group;
- (b) subjection the compound represented by formula (II) to catalytic hydrogen reduction by using a palladium catalyst, and
- treating the product with HX1,
- when R4 is an aryl-substituted methyl group.
11 more elements
An aminophenol compound represented by the following formula (III):
- wherein Y2 represents an N-alkyl-N-arylamino group, a diarylamino group, or a five-membered nitrogen-containing aromatic heterocyclic group having an endocyclic nitrogen atom bonded to the benzene ring, provided that when Y2 is a substituted diphenylamino group, it is a diphenylamino group having at least one substituent selected from a group consisting of alkyl, aryl, alkoxy, aryloxy, dialkylamino, N-alkyl-N-arylamino and diarylamino groups but not an N-(3-methylphenyl)-N-phenylamino group;
- R5, R6 and R7 each represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkoxy group or an aryloxy group;
- X2 represents an acid group of an inorganic or organic acid;
- and n is from 0 to 2.
1 more element
A nitrobenzene compound represented by the following formula (IV):
- wherein Y3 represents an N-alkyl-N-arylamino group or a diarylamino group, provided that when Y3 is a substituted diphenylamino group, it is a diphenylamino group having at least one substituent selected from among alkyl, aryl, alkoxy, aryloxy, dialkylamino, N-alkyl-N-arylamino and diarylamino groups;
- R8, R9, and R10 each represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkoxy group or an aryloxy group;
- and R11 represents a hydrogen atom or an alkyl group.
Dependencies are inferred from the claim text.